15,15-Diphenyl-2,3,4,5,6,8,9,11,12-octahydroimidazo[2,1-h][1,4,12]trioxa[7]thia[9]azacyclotetradecin-14(15H)-one

The title molecule adopts a cup-shaped conformation. In the crystal, layers lying parallel to the ab plane are formed by C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions.

The molecule adopts a cup-shaped conformation with the five-membered ring as the base and the C12-C17 benzene ring and the crown ether ring as the sides. This conformation is likely due to packing considerations since the three-dimensional structure is fairly compact with this arrangement (Fig. 2) but it may also be aided by the C5-H5BÁ Á ÁN2 hydrogen bond (Table 1 and Fig. 1). The five-membered ring is almost planar (r.m.s. deviation = 0.009 Å ) and the C12-C17 and C18-C23 benzene rings are inclined to it by 62.10 (7) and 61.35 (9) , respectively. The conformation of the crown ether ring places S1, O2 and O3 pointing away from the center of the molecule, but O4 points towards it. Intramolecular C-HÁ Á ÁO and C-HÁ Á ÁN interactions occur (Table 1). In the data reports crystal, zigzag chains of molecules extending along the a-axis direction are linked by C14-H14Á Á ÁO2 hydrogen bonds and these are connected into layers lying parallel to the ab plane by C6-H6AÁ Á ÁCg3 interactions (Table 1 and Fig. 2). The layers stack along the c-axis direction with normal van der Waals contacts (Fig. 3).

Figure 3
Elevation view of the layer structure seen along the b-axis direction with intermolecular interactions depicted as in Fig. 2.

Figure 2
Plan view of the layer structure viewed along the c-axis direction. C-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á(ring) interactions are shown by black and green dashed lines, respectively.

Figure 1
The title molecule with 50% probability ellipsoids. Intramolecular hydrogen bonds are depicted by dashed lines. Refined as an inversion twin Absolute structure parameter 0.25 (7) the presence of two equivalents of K 2 CO 3 (513 mg, 3.72 mmol). The reaction mixture was filtered while hot, and the solvent evaporated under reduced pressure. The residue obtained was dried and recrystallized from ethanol solution to yield colourless blocks of the title compound (Guerrab et al., 2018).

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal studied was refined as a two-component inversion twin with a refined BASF value of 0.25 (7).

data-1
IUCrData ( where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.42 e Å −3 Δρ min = −0.15 e Å −3 Absolute structure: Refined as an inversion twin. Absolute structure parameter: 0.25 (7) data-2 Special details Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 30 sec/frame was used. Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 -0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 -1.5 times those of the attached atoms. Refinement in Pna2 1 with SHELXL resulted in a Flack parameter of ca 0.25 and the message `inversion twin or centrosymmetric space group′. As the intensity statistics and PLATON ADSYMM did not support a centrosymmetric space group, the refinement was finished in Pna2 1 treating the model as an inversion twin with the addition of the instructions TWIN and BASF 0.25. The refined value of BASF was 0.25 (7).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.22326 (